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Sec. B] ADVANCES IN THE CHICHIBABIN REACTION 45 The amination of 1H-pyrrolo [2,3-f] isoquinoline (143)with excess sodium amide afforded 6-amino- 1H-pyrrolo[2,3-j'] isoquinoline (144)(Scheme 53) (84CHE399). The yield in xylene was 55% and in DMA it was 90%. The formation of 144 in liquid ammonia was observed by chromatography. Of the benzoquinolines, phenanthridine (14)was readily aminated in xylene or DMA to give 6-aminophenanthridine (15)(78RCR1042). Some derivatives of phenanthridine were aminated in xylene with sodium amide by Keene and Tissington (65JCS3032).
C SCHEME 26 350 sig QJQ /- QNH H 25% 10% I H 14% 10% SCHEME 21 7% 5% 14% 4% SCHEME 28 25% 15 % 7% 29% 29 ADVANCES IN THE CHICHIBABIN REACTION Sec. E] (73) (74 1 (75 1 SCHEME 29 SCHEME 30 D. AMINATION OF 5-METHYLPYRIMIDINE AND QUINOLINE Nitrogen heterocyclic systems other than pyridine also behave differently under pressure. 2: 1 (Scheme 29). 6: 1 (84EUP0098684A2). Quinoline (76) under pressure was converted to 2-amino-3,4-dihydroquinoline (77) as no hydrogen evolution was observed (Scheme 30) (84EUP0098684A2).
3 . AIkylaminution of Pyridine, 2- Picoline, 4- Picoline, and 2,6-Lutidine The various alkylaminations appear in Table IV. All were carried out by refluxing sodium sand in toluene containing the primary amine and catalyst until all or most of the sodium was consumed. The pyridine base was added in the second step with evolution of hydrogen (80UP1). 4. Alkyluminution of 4- Phenylpyrimidine In this lone example of alkylamination of a diazine, 4-phenylpyrimidine (29) was dissolved in boiling methylamine ( - 6°C) containing potassium 34 CHARLES K.
Advances in Heterocycling Chemistry. Vol. 44 by Author Unknown